CN104470891B - 用于合成鹅膏毒素结构单元及鹅膏毒素的方法 - Google Patents
用于合成鹅膏毒素结构单元及鹅膏毒素的方法 Download PDFInfo
- Publication number
- CN104470891B CN104470891B CN201380037459.2A CN201380037459A CN104470891B CN 104470891 B CN104470891 B CN 104470891B CN 201380037459 A CN201380037459 A CN 201380037459A CN 104470891 B CN104470891 B CN 104470891B
- Authority
- CN
- China
- Prior art keywords
- compound
- fmoc
- amatoxin
- resin
- generate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- SVYIDDYYJFBXSO-UWJYBYFXSA-N C[C@@H]([C@H](COC(C)=O)OC(C)=O)[C@@H](C(OC(C)(C)C)=O)N Chemical compound C[C@@H]([C@H](COC(C)=O)OC(C)=O)[C@@H](C(OC(C)(C)C)=O)N SVYIDDYYJFBXSO-UWJYBYFXSA-N 0.000 description 1
- 0 C[C@](C(C(OC(C)(C)C)=O)NC(C1(C2C1)N(*)C[C@@]2OC1=CC=CC=CC=CC=C1)=O)[C@](COC(C)=O)OC(C)=O Chemical compound C[C@](C(C(OC(C)(C)C)=O)NC(C1(C2C1)N(*)C[C@@]2OC1=CC=CC=CC=CC=C1)=O)[C@](COC(C)=O)OC(C)=O 0.000 description 1
- VJYUKAAGOCMCLU-UHFFFAOYSA-N OC(C(N(C1)C(OCC2c3ccccc3-c3c2cccc3)=O)=CC1OC1=CC=CC=CC=C1)=O Chemical compound OC(C(N(C1)C(OCC2c3ccccc3-c3c2cccc3)=O)=CC1OC1=CC=CC=CC=C1)=O VJYUKAAGOCMCLU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/065—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for hydroxy functions, not being part of carboxy functions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12005173.5 | 2012-07-13 | ||
| EP12005173.5A EP2684865A1 (en) | 2012-07-13 | 2012-07-13 | Methods for synthesizing amatoxin building block and amatoxins |
| PCT/EP2013/002084 WO2014009025A1 (en) | 2012-07-13 | 2013-07-12 | Methods for synthesizing amatoxin building block and amatoxins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104470891A CN104470891A (zh) | 2015-03-25 |
| CN104470891B true CN104470891B (zh) | 2016-10-12 |
Family
ID=48793164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380037459.2A Active CN104470891B (zh) | 2012-07-13 | 2013-07-12 | 用于合成鹅膏毒素结构单元及鹅膏毒素的方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US9676702B2 (es) |
| EP (2) | EP2684865A1 (es) |
| JP (2) | JP2015528799A (es) |
| KR (1) | KR102122575B1 (es) |
| CN (1) | CN104470891B (es) |
| AU (1) | AU2013289555B2 (es) |
| BR (1) | BR112015000232B1 (es) |
| CA (1) | CA2878081C (es) |
| CY (1) | CY1117950T1 (es) |
| DK (1) | DK2872479T3 (es) |
| ES (1) | ES2589306T3 (es) |
| HK (1) | HK1209723A1 (es) |
| HR (1) | HRP20160984T1 (es) |
| HU (1) | HUE029538T2 (es) |
| IL (1) | IL236129A (es) |
| MX (1) | MX361116B (es) |
| NZ (1) | NZ702752A (es) |
| PL (1) | PL2872479T3 (es) |
| PT (1) | PT2872479T (es) |
| RU (1) | RU2637924C2 (es) |
| SG (1) | SG11201500225WA (es) |
| SI (1) | SI2872479T1 (es) |
| UA (1) | UA116991C2 (es) |
| WO (1) | WO2014009025A1 (es) |
| ZA (1) | ZA201409384B (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3215519A1 (en) | 2014-11-06 | 2017-09-13 | Novartis AG | Amatoxin derivatives and conjugates thereof as inhibitors of rna polymerase |
| CN108495840A (zh) * | 2015-11-27 | 2018-09-04 | 海德堡医药研究有限责任公司 | γ-鹅膏菌素的衍生物 |
| EP3222292A1 (en) * | 2016-03-03 | 2017-09-27 | Heidelberg Pharma GmbH | Amanitin conjugates |
| EP3452492A1 (en) | 2016-05-05 | 2019-03-13 | Novartis AG | Amatoxin derivatives and conjugates thereof as inhibitors of rna polymerase |
| SG11201811290VA (en) | 2016-06-17 | 2019-01-30 | Magenta Therapeutics Inc | Compositions and methods for the depletion of cd117+cells |
| JP2019522050A (ja) | 2016-06-17 | 2019-08-08 | マジェンタ セラピューティクス インコーポレイテッドＭａｇｅｎｔａ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | 細胞の枯渇のための組成物および方法 |
| MX2019007604A (es) | 2016-12-23 | 2019-08-16 | Heidelberg Pharma Res Gmbh | Novedoso conjugado de amanitina. |
| WO2018134787A2 (en) | 2017-01-20 | 2018-07-26 | Magenta Therapeutics, Inc. | Compositions and methods for the depletion of cd137+ cells |
| JP7220199B2 (ja) | 2017-08-07 | 2023-02-09 | ハイデルベルク ファルマ リサーチ ゲゼルシャフト ミット ベシュレンクテル ハフツング | アマニチンの新規な合成方法 |
| EP3665173A1 (en) | 2017-08-07 | 2020-06-17 | Heidelberg Pharma Research GmbH | Novel method for synthesizing amanitins |
| AU2018317611B2 (en) * | 2017-08-18 | 2022-03-10 | Baili-Bio (Chengdu) Pharmaceutical Co., Ltd. | Non-natural amatoxin-type antibody conjugate |
| WO2019047941A1 (zh) * | 2017-09-08 | 2019-03-14 | 四川百利药业有限责任公司 | 鹅膏毒肽类抗体偶联物 |
| KR20190043031A (ko) * | 2017-10-17 | 2019-04-25 | 한국화학연구원 | 아마톡신 유도체 및 이의 제조방법 |
| EP3546447A1 (en) | 2018-03-29 | 2019-10-02 | Heidelberg Pharma GmbH | Synthesis of (2s,3r,4r)-4,5-dihydroxyisoleucine and derivatives |
| CA3107383A1 (en) | 2018-07-23 | 2020-01-30 | Magenta Therapeutics, Inc. | Use of anti-cd5 antibody drug conjugate (adc) in allogeneic cell therapy |
| SG11202110287QA (en) | 2019-04-24 | 2021-10-28 | Heidelberg Pharma Res Gmbh | Amatoxin antibody-drug conjugates and uses thereof |
| JP2022538692A (ja) * | 2019-07-05 | 2022-09-05 | プーレ バイオオーガニクス エスアイエー | α－アマニチン及びその誘導体の合成 |
| EP3792250A1 (en) * | 2019-09-13 | 2021-03-17 | Pure Bioorganics SIA | Synthesis of alpha-amanitin and its derivatives |
| KR102092817B1 (ko) * | 2019-08-22 | 2020-03-24 | 한국화학연구원 | 아마톡신 유도체 및 이의 제조방법 |
| CN112552196B (zh) * | 2020-11-23 | 2024-02-02 | 蚌埠丰原医药科技发展有限公司 | 一种制备赖氨匹林的方法 |
| WO2024121632A1 (en) | 2022-12-09 | 2024-06-13 | Crispr Therapeutics Ag | Use of anti-cd117 antibody drug conjugate (adc) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11137291A (ja) * | 1997-11-12 | 1999-05-25 | Mori Sangyo Kk | アマニチン類の製造法 |
| WO2010115629A2 (en) * | 2009-04-08 | 2010-10-14 | Deutsches Krebsforschungszentrum | Amatoxin-armed therapeutic cell surface binding components designed for tumour therapy |
| CN102387815A (zh) * | 2009-04-08 | 2012-03-21 | 海因茨·福尔斯蒂奇 | 用于治疗癌症的具鹅膏蕈毒素的靶结合部分 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1585076A (en) * | 1976-07-13 | 1981-02-25 | Roche Products Ltd | Peptides of phosphonic and phosphinic acids |
| DE4104024A1 (de) | 1991-02-09 | 1992-08-13 | Merck Patent Gmbh | Aminosaeurederivate |
| JPH0959228A (ja) * | 1995-08-17 | 1997-03-04 | Hokuriku Seiyaku Co Ltd | 光学活性なアミノアルコール及びその製造方法 |
| RU2169138C2 (ru) * | 1996-09-13 | 2001-06-20 | Ниппон Каяку Кабусики Кайся | Способ получения оптически активных эфиров эритро-3-амино-2-оксимасляных кислот и соответствующих исходных кислот |
| EP1077995A1 (en) | 1998-05-22 | 2001-02-28 | Abbott Laboratories | Antiangiogenic drug to treat cancer, arthritis and retinopathy |
| MXPA02009020A (es) * | 2000-03-17 | 2003-02-12 | Du Pont Pharm Co | Derivados de beta-aminoacidos ciclicos como inhibidores de las metaloproteasas de matriz y factor de necrosis de tumor alfa. |
| MXPA02010263A (es) | 2000-04-18 | 2004-08-12 | Lilly Co Eli | Proceso para preparar lipido ii. |
| ES2371085T3 (es) | 2006-05-27 | 2011-12-27 | Faulstich, Heinz, Dr. | Utilización de conjugados de amatoxinas o falotoxinas con macromoléculas para la terapia tumoral y de la inflamación. |
-
2012
- 2012-07-13 EP EP12005173.5A patent/EP2684865A1/en not_active Withdrawn
-
2013
- 2013-07-12 EP EP13737145.6A patent/EP2872479B1/en active Active
- 2013-07-12 KR KR1020157003282A patent/KR102122575B1/ko active IP Right Grant
- 2013-07-12 WO PCT/EP2013/002084 patent/WO2014009025A1/en active Application Filing
- 2013-07-12 MX MX2015000479A patent/MX361116B/es active IP Right Grant
- 2013-07-12 ES ES13737145.6T patent/ES2589306T3/es active Active
- 2013-07-12 BR BR112015000232-3A patent/BR112015000232B1/pt active IP Right Grant
- 2013-07-12 DK DK13737145.6T patent/DK2872479T3/en active
- 2013-07-12 JP JP2015520852A patent/JP2015528799A/ja active Pending
- 2013-07-12 PL PL13737145.6T patent/PL2872479T3/pl unknown
- 2013-07-12 CN CN201380037459.2A patent/CN104470891B/zh active Active
- 2013-07-12 PT PT137371456T patent/PT2872479T/pt unknown
- 2013-07-12 NZ NZ702752A patent/NZ702752A/en unknown
- 2013-07-12 SI SI201330268A patent/SI2872479T1/sl unknown
- 2013-07-12 HU HUE13737145A patent/HUE029538T2/en unknown
- 2013-07-12 UA UAA201501155A patent/UA116991C2/uk unknown
- 2013-07-12 US US14/414,143 patent/US9676702B2/en active Active
- 2013-07-12 CA CA2878081A patent/CA2878081C/en active Active
- 2013-07-12 AU AU2013289555A patent/AU2013289555B2/en active Active
- 2013-07-12 RU RU2015104802A patent/RU2637924C2/ru active
- 2013-07-12 SG SG11201500225WA patent/SG11201500225WA/en unknown
-
2014
- 2014-12-08 IL IL236129A patent/IL236129A/en active IP Right Grant
- 2014-12-19 ZA ZA2014/09384A patent/ZA201409384B/en unknown
-
2015
- 2015-10-22 HK HK15110372.0A patent/HK1209723A1/xx unknown
-
2016
- 2016-08-02 HR HRP20160984TT patent/HRP20160984T1/hr unknown
- 2016-08-22 CY CY20161100827T patent/CY1117950T1/el unknown
-
2018
- 2018-02-16 JP JP2018025844A patent/JP6560382B2/ja active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11137291A (ja) * | 1997-11-12 | 1999-05-25 | Mori Sangyo Kk | アマニチン類の製造法 |
| WO2010115629A2 (en) * | 2009-04-08 | 2010-10-14 | Deutsches Krebsforschungszentrum | Amatoxin-armed therapeutic cell surface binding components designed for tumour therapy |
| CN102387815A (zh) * | 2009-04-08 | 2012-03-21 | 海因茨·福尔斯蒂奇 | 用于治疗癌症的具鹅膏蕈毒素的靶结合部分 |
Non-Patent Citations (5)
| Title |
|---|
| A Large-Scale Preparation of (3S, 4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine and Its Analogs from L-Aspartic Acid;Toshihiko YOSHIDA等;《Chem. Pharm. Bull.》;19961231;第44卷(第5期);第1128-1131页 * |
| Synthesis of analogues of amaninamide, an amatoxin from the white Amanita virosa mushroom;GIANCARLO ZANOTTI等;《Int. J. Peptide Protein Res.》;19871231;第30卷;第450-459页 * |
| Th. Wieland等.Die absoluten Konfigurationen der in den Phytotoxinen enthaltenen γ-Hydroxyaminosä * |
| uren und der γ-Hydroxynorvaline.《Liebigs Ann. Chem.》.1968,第717卷第205-214页. * |
| 块磷鹅膏的培养条件及所产Amanitins毒素的分析;郭学武等;《微生物学报》;20060604;第46卷(第3期);第373-378页 * |
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| Date | Code | Title | Description |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |